Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
- Title
- Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
- Author
- 윤소원
- Keywords
- C-H AMINATION; PALLADIUM-CATALYZED REACTIONS; BETA-HYDRIDE ELIMINATION; INDOLE SYNTHESIS; INTERNAL ALKYNES; REGIOCONTROLLED SYNTHESIS; 4-SUBSTITUTED INDOLES; SUBSTITUTED INDOLES; COUPLING REACTIONS; CUPRIC CHLORIDE
- Issue Date
- 2015-04
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v. 13, NO 16, Page. 4652-4656
- Abstract
- Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn mu-hydrogen is made inaccessible or unavailable. In contrast to our previously reported beta-carbon elimination, cyclization of a variety of 2-alkenylaniline substrates under electrophilic palladium conditions unexpectedly afforded C3-substituted indoles. This unusual 1,2-migratory process was found to be operative across a variety of substrates with predictable migratory aptitude. A mechanistic proposal was put forward to rationalize the observed substrate dependence, and this unexpected finding could provide an opportunity for other related processes.
- URI
- http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00361J#!divAbstracthttp://hdl.handle.net/20.500.11754/23717
- ISSN
- 1477-0520; 1477-0539
- DOI
- 10.1039/c5ob00361j
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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